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Scott D. Clary Discusses Building a Brand, Hiring a Team, and Growing his Newsletter ROI Overload and Podcast Success Story

I'm of the opinion that if you put out incredible content into the world for free, money will come to you eventually.

- Scott D. Clary, ROI Overload & Success Story

Scott D. Clary is a career sales and marketing executive. His work has been featured in over 100+ news sites and publications. He speaks globally at industry conferences and has had articles and insights featured in Forbes, Wall Street Journal, Hackernoon, The Startup and others.

It would make sense then that he has ventured into the world of newsletters and podcasts to further share his knowledge. His newsletter, ROI Overload, is a daily look into growth trends & strategy, business, startups and technology. His podcast, Success Story, sits down with business leaders to unpack their story and share their wisdom. 

Continue reading to see how he balances his time between two growing (yet complimentary) media properties:


What inspired you to create ROI Overload and Success Story?

ROI Overload started as a news publication and then eventually morphed into a newsletter, because I liked the name. I found more value in building a newsletter and email list than building an entire news publication, because at the time, I was still working for a company. So I repurposed the domain into the newsletter I know run (on Substack) by the same name. 

For Success Story, I started it around the same time I started my newsletter, knowing that I wanted to build a brand around my name and I figured the best way to do that was to create as many pieces / types of content as possible. Podcast made the most sense, unpacking the stories of business leaders and using that as a content pillar. I now build my audience via newsletter, podcast, and social, but I use all mediums to cross pollinate. Podcast listeners go to my social, social checks out my podcast, newsletter checks out social, etc etc.

What does your research process consist of before interviewing your guests?

I find people who have achieved some level of success in business or a business adjacent topic and can unpack their own personal playbook / domain experience and teach something to my audience. It could be sales, marketing, business, entrepreneurship, hiring etc. Just people that are good teachers, so that the audience benefits.

Have you noticed any contributing factors for when interviews go better than expected? What about for ones that go worse than expected?

Speak about things that are top of mind for the guest. If you speak about something the guest isn't passionate about, then you won't get a good show out of them. When someone is excited about the thing they're talking about, that's when you get the best content.

What did the earliest versions of your newsletter/podcast look/sound like? How have they changed over time?

The first version of the newsletter was a publication, so it's pivoted significantly into a weekly newsletter. The content in the first version of my weekly newsletter is still very similar now though. I break down a business case study, and then highlight a tech, podcast and book the reader should check out.

The podcast first started as a sales / marketing focused podcast, and then I widened it a bit, to interview people who could teach/provide value to my audience but weren't exactly always a CMO/CRO. I realized if I wanted to grow the show, I needed to bring more people in and speak to a wider audience than just sales and marketing leaders.

What has been your go-to method for growing ROI Overload and Success Story?

Each definitely have their own strategy, but the high level strategy is cross platform promotion. Every newsletter I advertise my podcast, every podcast I put a link to subscribe to my newsletter in the show notes. People that find you on one platform, may not always find you on anther platform. Make discovery simple.

Also, you need to have a 1:1 content creation to distribution ratio at least. I spend just as much time posting my content, and publishing multiple times across all networks / channels as I do creating it. I think most people create and don't promote. If you build it, people don't always come, so you need to really push it out. Every newsletter / podcast goes out across linkedin, fb, tw, ig (stories) / in feed, quora, reddit, yt, hackernews, medium and I'm probably forgetting something, but you get the point (podcasts also go out across reels/tiktok/yt shorts).

What is the most challenging part of running a newsletter?

I would say the creative. I do a lot, including still run a sales/marketing team, so I sometimes try and squeeze writing into my evenings, and I can't think / don't have energy to write so for me the fix has been time blocking hours during my peak energy periods and dedicating that time to writing. 

For example, I do too much during the week, and I know that if I try and write during the week, the content will be sub-par, so I set time aside Sunday afternoon to write, when I have energy, and no distractions, then just schedule that for a Wednesday release.

How do you stay motivated when a piece seems to fall flat?

I've look for trends vs, short term results. When I see my subscriber count going up, that motivates me more than a single piece that flops. I really study people who are "successful" and when you look at how long they've been doing something (running a business, creating content, writing a newsletter, producing a podcast), you see that over the course of 5-10 years, if you stick with it, generally you will be successful at it. 

So I think it's more important to see if you're trending in the right direction, vs. being discouraged when a piece flops. For example, if you see you get 10 subscribers a day, you can do the math and model out where you'll be in 1-3-5 years (and you'll probably hit some level of exponential, hockey stick growth at some point as well), but still, model that out and realize that you literally just have to keep "doing" and you'll probably end up in a pretty good spot.

Do you have a team that helps with the promotion after you've created the content, or is it all you?

It started with just me, and then when I was able to monetize the podcast / newsletter I started hiring. So I now have a virtual assistant, video / audio editor, social media person and I hired a researcher/copywriter to launch a second daily newsletter.

But day 1... it was all me. I was editing video, creating social content, writing everything, posting everywhere.

Also, to touch on this point. This "do everything yourself" attitude really came from my day job, where I didn't want to hire someone, until I could figure out what "good" looked like, so when I run sales or marketing teams, I figure out what a good campaign looks like, good copy looks like, how to set up ads that convert etc, so when  I hire, I can at least have educated conversations with the professional who I brought onto my team. So I became very proficient in most everything, because it let me make better hiring decisions.

What tools do you use to research, create, and share your newsletter?

So part of why the newsletter is successful is because I speak about what I know. So the bulk of the newsletter is breaking down case studies of high growth tech companies. So when I read their story, and research how they grew, I can then dissect their strategy and provide context about "how" they got there, because I've lived it myself, (and used similar strategies) in my own companies growth. So the take away is... speak to what you know about, and build a tribe around that. I mean the companies I cover are huge tech giants so their stories are very public, Uber, Airbnb, Snowflake, Salesforce etc. So the info is just through google, and the context and insight is through my background and experience.

To share the newsletter I use Substack, to monetize I use paved (I partnered with them so use my aff link lolol), um.. I use IFTTT for auto posting.

I also post my newsletter on my website and medium to increase the reach, (and on the site, act as seo-able, content).

How many hours per week do you spend working on your newsletter and podcast? How often do you experiment with your routines around making each?

I spend about 8 hours a week on the newsletter and podcast, so it's significant, but you don't need to put that much in. I record 2x podcast episodes a week and write 1 newsletter a week and still manage a team that now supports me. Before I hired a team it was 1x newsletter every 2 weeks and 1x podcast a week and that was still about 8 hours. 

I play around with my routine any time I hire or find a new tool that optimizes my workflow. If I have budget, then I'll try and outsource more (aka if more ad dollars come in), if not then I'll only revamp my routine if I find a new piece of tech that does something better than what I'm already using. I also live on product hunt and app sumo to scope out the latest and greatest tech for creators. 

I also try and block off hours, so I spend 3-4 hours Sunday creating newsletter, and setting up podcasts for the week, reviewing the show notes etc. And then 3-4 hours throughout the week posting everywhere. I pre schedule some of my social, but not all of it (use buffer for that). 

Was there any advice that you heard frequently when you were starting your newsletter that turned out not to be helpful? If you could give one piece of advice to someone starting a newsletter they intended to monetize, what would you say?

I think people try and monetize too soon. I think people try and set up subscription content too soon and overvalue their content. I'm of the opinion that if you put out incredible content into the world for free, money will come to you eventually. 

I rather build a huge audience and have that then have a tiny audience and have all gated content, and free content really does help you build a huge audience. And if you're just starting out, I think distribution and awareness should be the goal, not money day 1. Which is also why I think side hustles are so important. Don't do this full time, do it part time while at your day job, and don't feel the need to risk your livelihood. Almost anyone could put out 2x podcasts a month an 2x newsletters a month, and not significantly impact their free/family time. Ramp up when you have content that resonates and you start having the ability to monetize, then you've essentially found product market fit for your side hustle.

Also, second piece of monetization advice. If you really want to monetize. Run automated campaigns with a sales pitch, and your newsletter numbers, so that you don't need to spend too much of your time selling. You can use broker services like paved for newsletters, advertisecast for podcasts or just sign up for a tool like apollo and run campaigns, pitching your newsletter or podcast to marketing managers/directors at larger companies in your niche. You'll get bites and it wont take up too much of your time.

The goal is to find a way to not let this consume your entire life, until it's replacing your job.

Of course, if you did full time sales, you'd get some deals and probably make a bit more money, but it's all about getting optimal value out of your time, so find tools to scale yourself until you can justify spending more time on whatever thing you're creating.

Once you've found people to interview for your podcast, how do you convince them to come on?

I'm a sales person by trade so bringing people on was pretty simple. I just identified the value my show has, and why they'd want to be on it. At the beginning when I didn't have as large an audience I identified my value prop as being able to create content for their social, so I said if they came on I'd create social clips from the show for them, that they could post on their own social platforms.

I still do that, but now I can win them over by speaking to the size of my audience they can tap into.

What newsletters and blogs do you read most frequently?

I love James Clear's newsletter(productivity & habits) & First 1000(startups & growth). There's a few but those are my ones that I read almost every week.

Who is the dream guest that you want to interview for your show, but haven't had a chance to speak to yet?

I would say Branson/Musk/Bezos. I'm starting to get bigger business names on, but for a biz show - those are the epitome of who I'd want to bring on.

What are your next milestones for your newsletter and podcast?

Newsletter, I think I just want to use it as a medium to connect on a more meaningful level with my followers / subs. I can chat about things that matter to me and really just keep that as a way of communicating directly with people that really love my content. I haven't really set a vision for that one yet, because my main focus is my podcast.

That being said, I'm not naive to the fact that the larger the subscriber list is, the more money I can charge for sponsorship, so I'm just going to focus on growing that at the same pace as what it's already growing at.

For the podcast, I'm really doubling down on that. I want to get a studio, start recording in person. It was just brought into the hubspot podcast network so I'm super excited about that. In person / video interviews will be the next step, and I'd ideally like it to eventually compete with Tim Ferris in terms of the size of the show. So I really want to be a name in the space and I think I'll keep pushing until I get there.